Chirality & Odour Perception
John C. Leffingwell, Ph.D.

The 4-Acetoxyfuraneols

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Photo by permission of M. Roudintska - Art & Parfum

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(S)-(-)-4-Acetoxyfuraneol - weak caramelic odor

= (-)-(5S)-2,5-dimethyl-4-oxo-4,5-dihydrofuran-3-yl acetate or (-)-(2S)-2,5-dimethyl-3-oxo-2,3-dihydrofuran-4-yl acetate

Ref: Makoto Emura, Yoshihiro Yaguchi, Atsufumi Nakahashi, Daisuke Sugimoto, Nobuaki Miura and Kenji Monde, Stereochemical Studies of Odorous 2-Substituted-3(2H)-furanones by Vibrational Circular Dichroism, J. Agric. Food Chem., 2009, 57 (21), pp 9909–9915

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(R)-(+)-4-Acetoxyfuraneol - burnt, intense caramel odor

= (+)-(5R)-2,5-dimethyl-4-oxo-4,5-dihydrofuran-3-yl acetate or (+)-(2R)-2,5-dimethyl-3-oxo-2,3-dihydrofuran-4-yl acetate

Ref: Makoto Emura, Yoshihiro Yaguchi, Atsufumi Nakahashi, Daisuke Sugimoto, Nobuaki Miura and Kenji Monde, Stereochemical Studies of Odorous 2-Substituted-3(2H)-furanones by Vibrational Circular Dichroism, J. Agric. Food Chem., 2009, 57 (21), pp 9909–9915

Cyclic Terpenoid Odorants

Bicyclic Terpenoid Odorants

Acyclic Terpenoid Odorants

Ionones, Irones, Damascones & Structurally Related Odorants

Acyclics (Alcohols, Esters, Acids, Aldehydes)

Lactones

Sesquiterpenoid Related Odorants

Steroid Urine Type Odorants

Sandalwood Type Odorants

Musk Odorants

Miscellaneous

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